Predicting a reaction between ester and acyl halide

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The discussion centers on the reaction of aminobenzoic acid with ethanol to form an ester, which then reacts with acyl chloride (CH3COCl). One participant suggests that this could lead to a Friedel-Crafts acylation product, indicating that electrophilic addition to the benzene ring could occur at ortho or para positions, although typically this requires a catalyst. However, the initial configuration of the aminobenzoic acid is crucial for determining the product. Another participant proposes that a more likely outcome is the formation of an amide through an addition-elimination mechanism, where the amino group acts as the nucleophile and chloride is eliminated.
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HI ppl, I have a question here. I deduced a forumla of an acid, aminobenzoic acid and this reacted with ethanol to give the corresponding ester. This ester then reacts with an acyl halide, CH3COCl, any ideas as to the product of this reaction? Thanks, Joe
 
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You may have a friedel craft acylation product of some sort...electrophilic addition to the benzene, ortho/para (although I've not seen this done w/o a catalyst). It all should depend on what your initial configuration of aminobenzoic acid is...as far as I'm concerned, this can be ortho/para and even meta.

A better suggestion is the formation of an amide through addition-elimination, amino group as the nucleophile and elimination of chloride anion.
 

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